Abstract
The efficiencies of hydrogen peroxide derivatives in the Baeyer–Villiger oxidation of cyclopentanone to δ-valerolactone have been compared. The oxidants used were hydrogen peroxide in acetic, formic, or trifluoroacetic acid, magnesium and sodium monoperoxyphthalates, cumene hydroperoxide, and tert-butyl hydroperoxide. The oxidation was carried out in water, aqueous methanol, and water–ethyl acetate. Sodium and magnesium monoperoxyphthalates turned out to provide high conversion and selectivity under mild conditions.
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REFERENCES
Okada, M., Prog. Polym. Sci., 2002, vol. 27, p. 87. https://doi.org/10.1016/S0079-6700(01)00039-9
Yang, J., Jia, L., and Hao, Q., J. Macromol. Biosci., 2005, vol. 5, p. 896. https://doi.org/10.1002/mabi.200500096
Lendlein, A. and Sisson, A., Handbook of Biodegradable Polymers: Synthesis, Characterization, and Applications, New York: Wiley, 2011.
Tian, H., Tang, Z., Zhuang, X., Chen, X., and Jing, X., Prog. Polym. Sci., 2012, vol. 37, p. 237. https://doi.org/10.1016/j.progpolymsci.2011.06.004
Friess, S.L. and Farnham, N., J. Am. Chem. Soc., 1950, vol. 72, p. 5518. https://doi.org/10.1021/ja01168a042
Yin, G.Z. and Yang, X.M., J. Polym. Res., 2020, vol. 27, p. 38. https://doi.org/10.1007/s10965-020-2004-1
Meinwald, J. and Frauenglass, E., J. Am. Chem. Soc., 1960, vol. 82, p. 5235. https://doi.org/10.1021/ja01504a052
Monson, R.S., Advanced Organic Synthesis: Methods and Techniques, New York: Academic, 1971.
Kennedy, R. and Stock, A., J. Org. Chem., 1960, vol. 25, p. 1901. https://doi.org/10.1021/JO01081A019
Strukul, G., Angew. Chem., Int. Ed., 1998, vol. 37, p. 1198. https://doi.org/10.1002/(SICI)1521-3773(19980518)37:9<1198::AID-ANIE1198>3.0.CO;2-Y
Piscopo, C., Löbbecke, S., Maggi, R., and Sartori, G., Adv. Synth. Catal., 2010, vol. 352, p. 1625. https://doi.org/10.1002/adsc.201000076
Vagnoni, M., Samorì, C., Pirini, D., Vasquez De Paz, M.K., Gidey, D.G., and Galletti, P., Biocatal. Biotransform., 2021. https://doi.org/10.1080/10242422.2021.1913126
Mino, T., Masuda, S., Nishio, M., and Yamashita, M., J. Org. Chem., 1997, vol. 62, p. 2633. https://doi.org/10.1021/jo9623043
Kuznetsov, V.A., Pervova, M.G., and Yatluk, Yu.G., Russ. J. Appl. Chem., 2013, vol. 86, p. 191. https://doi.org/10.1134/S1070427213020080
Dech, V., Mates, M., Khonig, Kh., and Vazem, G., RU Patent no. 2174490, 1997.
Hignett, G.J., US Patent no. 4403994, 1983.
Analiticheskaya khimiya: Metody khimicheskogo analiza (Analytical Chemistry: Methods of Chemical Analysis), Petrukhin, O.M., Moscow: Khimiya, 1992.
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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 4, pp. 381–386 https://doi.org/10.31857/S0514749222040024.
This article is published according to the report presented at the Vth International Conference “Modern Synthetic Methodologies for the Design of Drugs and Functional Materials” which was held on November 8–12, 2021, in Yekaterinburg and Perm.
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Solovyova, Y.V., Puzyrev, I.S., Pervova, M.G. et al. Synthesis of δ-Valerolactone Using Stable Hydrogen Peroxide Derivatives. Russ J Org Chem 58, 480–483 (2022). https://doi.org/10.1134/S1070428022040029
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DOI: https://doi.org/10.1134/S1070428022040029